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Consolidated Statements of Cash Flows (Unaudited) - USD ($)
$ in Thousands
 9 Months Ended
Sep. 30, 2020
Sep. 30, 2019
Cash flows from operating activities:    
Net loss $ (69,931) $ (39,499)
Adjustments to reconcile net loss to net cash provided by (used in) operating activities:    
Depreciation and amortization 16,347 11,969
Amortization of debt discount and issuance costs 12,213 7,783
Stock-based compensation expense 46,921 29,490
Provision for doubtful accounts 1,760 1,782
Deferred income taxes 0 (761)
Foreign currency re-measurement loss 308 570
Other non-cash (income) expense (87) (1,635)
Changes in operating assets and liabilities:    
Accounts receivable 13,228 10,860
Deferred contract acquisition and fulfillment costs (5,278) (5,403)
Prepaid expenses and other assets 1,352 (9,878)
Accounts payable 1,922 1,132
Accrued expenses (3,079) (4,822)
Deferred revenue (10,456) (12,124)
Other liabilities (915) 1,292
Net cash provided by (used in) operating activities 4,305 (9,244)
Cash flows from investing activities:    
Business acquisition, net of cash acquired (125,826) (14,607)
Purchases of property and equipment (7,125) (27,053)
Capitalization of internal-use software costs (4,407) (4,686)
Purchases of investments (108,710) (114,208)
Sales/maturities of investments 155,599 177,287
Net cash (used in) provided by investing activities (90,469) 16,733
Cash flows from financing activities:    
Proceeds from issuance of convertible senior notes, net of issuance costs paid of $7,201 222,799 0
Purchase of capped calls related to convertible senior notes (27,255) 0
Deferred business acquisition payment (150) 0
Payments of debt issuance costs (411) 0
Taxes paid related to net share settlement of equity awards (5,984) (4,926)
Proceeds from employee stock purchase plan 7,082 5,521
Proceeds from stock option exercises 6,219 7,924
Net cash provided by financing activities 202,300 8,519
Effect of exchange rate changes on cash, cash equivalents and restricted cash 160 (648)
Net increase in cash, cash equivalents and restricted cash 116,296 15,360
Cash, cash equivalents and restricted cash, beginning of period 123,413 99,565
Cash, cash equivalents and restricted cash, end of period 239,709 114,925
Supplemental cash flow information:    
Cash paid for interest on convertible senior notes 2,875 2,779
Cash paid for income taxes, net of refunds 333 404
Non-cash investing activities:    
Leasehold improvements acquired through tenant improvement allowance 0 14,016
Reconciliation of cash, cash equivalents and restricted cash:    
Total cash, cash equivalents and restricted cash $ 239,709 $ 114,925